Oxy containing tertiary amine oxides



United States Patent .0

- 3,202,714 UXY CQNTAHJTNG TERTEARY AMENE (BXHDES Roger E. Zimmerer,Springfield Township, Hamilton County, and Howard F. Drew, Wyoming,Ohio, assignors to The Procter a Gamble (Iompany, Cincinnati, Qhio, acorporation of Uhio No Drawing. Filed Dec. 4, 1961, Ser. No. 156,9? 6Claims. (Cl. 260-584) This invention relates to novel tertiary amineoxide detergents and detergent compositions containing them.

in the constant improvement of organic detergent compounds, certainfeatures have been found to be highly desirable. These features includeresistance toward the ingredients imparting hardness to water, a highdegree of detergency, and capacity for solubilization of hard watersoaps, such as calcium soap. Although there are a number of organicdetergents which have these characteristics, detergent compounds havingadditional desirable characteristics find a wider scope of application.

Thermal stability is a hi hly desirable property which is lacking inmany detergents. Such stability is particularly desirable whendetergents are subjected to heat during use or processing, as forexample, in spray drying granular detergent compositions.

Another advantageous property for an organic detergent is a low degreeof hygroscopicity which results in improved crystallinity. Whendetergent surface active agents which are hygroscopic are used in bar orgranular cool water to retain their crease resistant properties.

Wool garments should be washed in cool water. locations warm or hotWater is not available.

It is a principal object of this invention to provide organic detergentsand detergent compositions which have excellent detergencycharacteristics as Well as high thermal stability and a low degree ofhygroscopicity. It is another important object to provide detergents anddetergent compositions which have these characteristics and also have ahigh degree of detergency in cool Water.

In some It was found that these and other objects are achieved i in anovel class of tertiary amine oxides having the structure set forthbelow and in detegrent compositions containing such compounds,preferably in solid form, as hereinafter more fully described.

The amine oxides of this invention are:

Inthe above formulas, R is an alkyl, 2-hydroxyalkyl, 3-hydroxyalky1 or3-alkoxy-2-hydroxypropyl radical in which the alkyl and alkoxy,respectively, range from 10 to 18 carbon atoms in chain length, R and Rare each methyl, ethyl, propyl, isopropyl, 2-hydroxyethyl,2-hydroxypropyl or 3-hydroxypropyl groups and at least one of the R andR radicals contains a hydroxy group. The class of compounds describedabove will hereinafter be referred to more simply as R1R2R3N O.

Examples of the compounds of this invention arebis(2-hydroxyethyl)dodecylamine oxide, bis(2-hydroxyethyl)-2-hydroxytetradecylarnine oxide, (2-hydroxyeth-.

yl)methyltetradecylamine oxide, bis(3-hydroxypropyl)-3-hydroxyhexadecylamine oxide, (2 -hydroxyp1'opyl)-2-hydroxyoctadecylpropylamine oxide, bis(2-hydroxyethyl)-3-hydroxyhexadecylamine oxide, bis(2-hydroxypropyl)do decylamine oxide,bis(Z-hydroxyethyl)-3-hydroxydo'decy-lamine oxide,bis(2-hydroxyethyl)-2-hydroxydodecylamine oxide, N,N-bis(2 hydroxyethyl)3-dodecoxy-2-hydroxypropylamine oxide and N-methyl-N-(2-hydroxyethyl)-3tetradecoxy-2-hydroxypropylamine oxide.

Tertiary amine oxides as a broad class of compounds are known. It wassurprising to find, however, that the particular trialkylamine oxidescontaining particularlyplaced hydroxy groups as described above (i.e., ahydroxy group in R and/ or R have such highly desirable properties foruse as organic detergents, i.e., improved hygroscopicity, thermalstability and cool water detergency characteristics.

It appears that only certain tertiary amine oxides have theaforementioned desirable characteristics; in these certain amine oxides,R R and R must be as described above. If the alkyl or allroxy in R islonger in chain length than 18 carbon atoms or shorter in chain lengththan 10 carbon atoms, desired detergency is not obtained. Likewise, if Rand R contain more than 3 carbon atoms, such characteristics are notobtained. Either R or R must contain a hydroxy group in the 2 or 3position, Whether or not R contains a hydroxy group, in order to achieveimproved thermal stability, hygroscopicity and, especially, cool-waterdetergency characteristics. These properties are particularlyoutstanding when both R and R contain a hydroxy group. containinghydroxymethyl groups are not stable.)

In particular, those tertiary amine oxides wherein R is a C C alkyl, C-C Z-hydroxyalkyl, C C 3- hydroxyalkyl or C -C 3-alkoxy-2-hydroxypropylradical and both R and R are 2-hydroxyethyl radicals have cool waterdetergency properties markedly superior to conventional organicdetergent active ingredients such as sodium' dodecylbenzenesulfonate(the dodecyl group being derived fromtetrapropylene). Especiallyoutstanding is bis(2- hydroxyethyl)dodecylamine oxide; this compoundalso has excellent sudsing properties.

As regards the compounds in which there is an hydroxy group in the long"chain R radical, hydroxy groups in the 2 or 3 position in R provideimproved skin-mildness, thermal stability and hygroscopicitycharacteristics (compared to an unsubstituted 'R alkyl group). Theimproved mildness, thermal stability and hygroscopicity characteristicsof amine oxide compounds containing hydroxy groups in R but not in R orR is set forth in copending application of Howard F. Drew, Serial No.156,993, tiled concurrently herewith. The improved thermal stability andhygroscopicity characteristics provided by hydroxy groups in R are inaddition to these characteristics which are provided by hydroxy groupsin R and/ or R Thus, the mildness, hygroscopicity and thermal stabilitycharacteristics of the tertiary amine oxides which have a hydroxy groupin all three alkyl radicals (e.g., bis(2-hydroxyethyl)-2-hydroxydodecylamine oxide and N,N-bis(2-hydroxyethyl)-3-dodecoxy-2 hydroxypropylamine oxide) are betterthan those compounds which contain hydroxy groups only in the R and/ orR radicals or in those compounds which contain no hydroxy groups.Improved cool water detergency is, however, dependent on the presence ofhydroxy groups in R and/ or R 7 In tertiary amine oxides of thisinvention, the alkyl or alkoxy in the R group can be derived fromnaturally occurring fats and oils or from synthetic sources. Mixtures ofamine oxides are very suitable wherein the alkyl or alkoxy inR varies inchain length in the C to C (Tertiary amine oxidesrange, as for example,the alkyl or alkoxy groups derived from coconut fatty alcohol (ordistilled coconut fatty alcohol). Those amine oxides in which the alkylor alkoxy in R ranges from 12 to 14 carbon atoms are preferred. The3-alkoxy-2-hydroxypropyl R radical has the following general formula:

R 011233110 Hrwherein R ranges from 10 to 18 carbon atoms in chainlength.

The tertiary amine oxides of this invention can be prepared, in general,by oxidizing the corresponding tertiary amine. See, for example, BritishPatent 437,566. The corresponding tertiary amine, in general, can beprepared by alkylating, with an appropriate long chain alkyl compound,the appropriate secondary amine. The examples explain in detail suchreactions. The preparation of alkyl glycidyl ethers (a source of the3-alkoxy-2-hydroxypropyl R is described in Canadian Patent 582,404 andU.S. Patent 2,989,547.

Compounds of this invention are useful per se as detergents and surfaceactive agents. Desirably they are used with other materials to formdetergent compositions, particularly solid form compositions as forexample, bar, flake, granular or tableted granular compositions. (Thetertiary amine oxide of this invention can also be used to make liquiddetergent compositions.) Such detergent compositions can contain fromabout 5% to about 80% of the tertiary amine oxides of this invention andfrom about 95% to about 20% of anionic organic detergents, nonionicorganic detergents, water soluble inorganic alkaline builder salts,water soluble organic alkaline sequestrant builder salts or mixturesthereof.

Granular or flake detergents preferably contain about 5% to about 50% ofthe amine oxides of this invention and from about 95% to about 50%normally solid, water soluble inorganic alkaline builder salts, or watersoluble organic alkaline sequestrant builder agents. Bar formulationscontain about 5% to about 50% of the amine oxides of this invention whenused with anionic detergents, such as a soap base, and, if desired,alkaline inorganic or organic builders or inert fillers. Barformulations can contain about 40% to about 80% of the amine oxides ofthis invention as the only detergent component, if desired, and thebalance inert fillers or builders.

Anionic organic detergents used alone or in admixture include both thesoap and non-soap detergents. Examples of suitable soaps are the sodium,potassium, ammonium and alkylolammonium salts of higher fatty acids (C CParticularly useful are the sodium and potassium salts of the mixturesof fatty acids derived from coconut oil and tallow, i.e., sodium orpotassium tallow and coconut soap. Examples of anionic organic non-soapdetergents are: alkyl glyceryl ether sulfonates; alkyl sulfates; alkylmonoglyceride sulfates or sulfonates; alkyl polyethenoxy ether sulfates;acyl sarcosinates; acyl esters of isethionates; acyl N-methyl taurides;alkylbenzenesulfonates; alkyl phenol polyethenoxy sulfonates. In thesecompounds the alkyl and acyl groups, respectively, contain 10 to 20carbon atoms. They are used in the form of water soluble salts, thesodium, potassium, ammonium and alkylol-ammonium salts, for example.Specific examples are: sodium lauryl sulfate; potassium N-methyl lauroyltauride; triethanolammonium dodecylbenzenesulfonate. I

The examples of nonionic organic detergents are: polyethylene oxidecondensates of alkyl phenols wherein the alkyl group contains from 6 to12 carbon atoms (e.g., 5- octylphenol) and the ethylene oxide'is presentin a molar ratio of ethylene oxide to alkyl phenol in the range of 10:1to :1; condensation products of ethylene oxide with the productresulting from the reaction of propylene oxide and ethylene diaminewherein the molecular weight of the condensation products range fromwater.

5000 to 11,000; the condensation product of from about 5 to 30 moles ofethylene oxide with one mole of a straight or branched chain aliphaticalcohol containing from 8 to 18 carbon atoms (e.g., lauryl alcohol).

Water soluble inorganic alkaline builder salts used alone or inadmixture are alkali metal carbonates, borates, phosphates,polyphosphates, bicarbonates and silicates. (Ammonium or substitutedammonium salts can also be used.) Specific examples of such salts aresodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodiumpyrophosphate, sodium bicarbonate, potassium tripolyphosphate, potassiumpyrophosphate, sodium hexametaphosphate, sodium sesquicarbonate, sodiummonoand di-ortho phosphate and potassium bicarbonate. Such inorganicbuilder salts enhance the detergency of the subject amine oxides.

Examples of water soluble organic alkaline sequestrant builder saltsused alone or in admixture are alkali metal, ammonium or substitutedammonium amino polycarboxylates, e.g., sodium and potassiumethylenediaminetetraacetate, sodium and potassiumN-(Z-hydroxyethyl)-ethylenediaminctriacetates, sodium and potassiumnitrilotriacetates and sodium potassium, and triethanolammoniumN-(2-hydroxyethyl)nitrilodiacetates. Other organic alkaline sequestrantbuilder salts which can be used are:hydroxyethylethylenediaminetriacetates; 2-hydroxyethyliminodiacetates;diethylenetriaminepentaacetates; 1,Z-diaminocyclohexanetetraacetates.Mixed salts of these polycarboxylates are also suitable. The alkalimetal salts of phytic acid, e.g., sodium phytate are also suitable asorganic alkaline sequestrant builder salts (see U.S. Patent 2,739,942).

Preferred detergent compositions contain about 10% to about 30% of thetertiary amine oxides of the invention and at least an equal amount ofsodium tripolyphosphate. Desirably the bis(2-hydroxyethyl)alkylamineoxides wherein the alkyl radical ranges from 12 to 14 carbon atoms inchain length are used in such preferred compositions.

The detergent compositions of this invention can contain any of theusual adjuvants, diluents and additives, for example, ampholytic orzwitterionic detergents, cationic deposition agents, bacteriostaticagents, dyes, fiuorescers, oxygen or chlorine bleaches, suds builders,suds depres sors and the like.

The following are examples which illustrate the tertiary amine oxidecompounds and compositions of this invention.

EXAMPLE I grams of dodecyl bromide, 260 grams of diethanolamine and 250ml. of methanol were mixed together in a one liter bomb which was sealedand rocked for 15 hours at C. The mixture was removed from the bomb anddiluted with suflicient water to obtain a 60:40 water to alcohol solventratio. The solution was then made basic with sodium hydroxide. The longchain alkyl derivatives in the basic mixture were extracted withpetroleum ether. The petroleum ether mixture was then acidified withdilute HCl; unreacted alkyl bromide was extracted with petroleum ether.The water layer was removed and made basic. The tertiary amine in thebasic water solution was extracted with ethyl ether. This reaction isrepresented by the following equation:

The yield of the bis(2-hydroxyethyl)dodecylamine was 98%. The materialhad an amine number of 208 while 205 is calculated.

55 grams of this tertiary amine were mixed with 13.6 grams of hydrogenperoxide (45.3 grams of 30% aqueous H 0 solution), 75 ml. of ethanol and75 ml. of The mixture was heated 'at 60 C. for 7 hours with constantagitation. The solution was cooled to room temperature and excesshydrogen peroxide was The-material had the following elemental analysiscompared with the calculated analysis.

Found Calculated I .4 66.1 66. o n 12.2 12.7 N 4.6 4.81 0 (bydifierence) L 17. 1 16.49

In a cloth-swatch detergency. test, the bis(2-hydroxyethyl)dodecylamineoxide was substantially superior to sodium dodecylbenzenesultonate .(awidely used detergent. active for laundering compositions). This testinvolved Washing naturally soiled cloth (desized print cloth) in a 0.1%aqueous solution of a composition comprising 20% organic detergentcompound (amine oxide being tested or the alkyl benzenesulfonatestandard), 50% sodium tripolyphosphate and 30% sodium sulfate. Thecomposition had a pH of 10.0 and the washing was done at 130 F. for 10minutes using wash water of 7' grains per gallon hardness. Thedetergency effectiveness was determined by measuring the percentage oflipid soil remaining on a standard size swatch (on a dry basis) afterthe washing operations. The percentage of lipid soil remaining afterwashing with the amine oxide test composition was compared with thepercentage after washing with the alkylbenzenesulfonate standardcomposition. 0n the basis of the percent residual lipid soil, the lowerthe percent, the better the detergency performance. A Tergotometer wasused for the washing operation; (Tergotometer testing is described inDetergency Evaluation and Testing, by J. C. Harris, IntersciencePublishers, Inc. (1954) page 60.)

The hygroscopicity of bis(2-hydroxyethyl)dodecyl amine oxide wasdetermined by exposing dry recrystallized material in a constant 50%relativehumidity chamher at 70 F.; it had weight increases of 3% after 1day and 6% after 7 days in this hygroscopicity test.Dimethyldodecylamine oxide had weight increases of 32% after 1 day and30% after 7 days. It is apparent that the former compound is much lesshygroscopic than the latter; thus the former compound is preferred forsolid form detergent compositions. Bis(2-hydroxyethyl)dodecylamine oxidedecomposed at a temperature in the range of 135 C. to 150 C. whereasdimethyl-dodecylamine oxide decomposed at 110, C. The formercompoundtherefore is preferred for spraydried detergent compositions. Yf

Bis(2-hydroxypropyl)tetradecylamine oxide, bis(2-hydroxyethyl)hexadecylamineoxide and bis(2-hydroxyethyl)-stearylamineoxide can be made by processes simi lar to that described in Example I.These compounds Will havesubstantially equivalentthermal stability andhygroscopicity characteristics and the detergency efficacy will beslightly less than that of the dodecyl compounds.

The bis(2-hydroxyethyl)stearylamine oxide is especially suitable. forasolid form detergent composition-such as atoiletbar. I

' EXAMPLE II 28 grams of 1,2-epoxydodecane, 79 grams of diethanol amineand one gram of anhydrous'aluminum chloride were placed in a 300 ml.bomb. The bomb was sealed and'rocked for hours at 200 C. Thebombwascooled and opened; the'contents were added to aqueous solution of HCl(about 2 moles). The unreacted epoxya dodecane in the acidified reactionmixture was then extracted with petroleum ether. The remaining aqueoussolution was made alkaline; the tertiary. amine was then extracted fromthe alkaline solution with petroleum ether. Analysis of the resultingbis(Z-hydroxyethyl)-2-hydr0xydodecylamine after distillation indicated a70% yield.

This reaction is represented by the following equation:

D.C1UH21OHOH2 HN(CH4OH)3 HC10Hz1CHCHgN(CgH OH)g (5H 20 grams of thebis(Z-hydroxyethyl)2-hydroxydodecyl amine were mixed with 5.1 grams of H0 (17 grams 30% aqueous solution) and 25 ml. of ethanol. The mixture wasstirred and heated at 60 C. for 5 hours and then allowed to standovernight at room temperature. The resulting solution was then dilutedwith 300 ml. of water. The excess H 0 was decomposed with powderedplatinum black. The mixture was filtered to remove the platinum black;the unreacted amine was extracted two times with 300 ml. of petroleumether. The remaining aqueous solution was freeze dried to yield 20 gramsof amine oxide and representing a 93% yield. The oxidation reaction isrepresented by the following equation:

n-C H CHCH N(C H40H) H 0 I1 CIOH21C IOHZN(CH2H4OH)2 1120 OH O Theelemental analysis of this tertiary amine oxide compared with thetheoretical analysis, is as follows:

Found Calculated C 62.6 62.8 H 11.3 11.6 N 4.55 4.57 O (by difference)21.55 21.03

Bis(2-hydroxyethy1)-2-hydroxydodecylamine oxide was tested by the clothswatch test described in Example I and found to have a detergencyeffectiveness substantially superior to that of sodiumdodecylbenzenesulfonate and approaching the hot F.-t F.) waterdetergeney of sodium tallow alcohol sulfate which is one of the bestcommercially used laundry detergent active ingredients.

Bis(2-hydroxyethyl)-2-hydroxydodecylamine oxide had Weight increases -of1% (1 day and 7 days) in the hygroscopicity test described in Example Iand decomposed at a temperature in the range of 135 C. to C.

' EXAMPLE I11 One mole of diethanolamine (420 grams) was reacted withone mole of alkyl glycidyl ether (1020 grams), wherein the alkyl groupwas derived from distilled coconut oil fatty alcohol (2% C 66% C 23% C9% C at 300 F. for 1%. hours at atmospheric pressure. The reaction isrepresented by the following equation: 1

540 grams of the resulting N, N-bis(2-hydroxyethyl) 3-coconutalkoxy-Z-hydroxypropylamine was reacted with 255 grams of 30% aqueoushydrogen peroxide and 1205 grams of water at F for 1 /2 hours. Theexcess hy-' drogen peroxide was allowed to decompose under room storageconditions, The resulting.N,N-bis(2-.hydroxyethyl)-3-coconutalkoxy-Lhydroxypropylamine oxide had Iexcellent detergency characteristics, particularly. in built detergentformulations used in"80 F. Wash water. The

and thermal stability. It is also substantially milder to 7 the humanskin as compared to unsubstituted amine oxide such asdimethyldodecylamine oxide.

In addition to the cloth swatch test described in Example I, thedetergency of the amine oxides of this invention was evaluated bywashing naturally soiled white dress shirts. Shirts were worn by malesubjects under ordinary conditions for two normal working days. Thedegree to which a detergent composition containing a detergent compoundto be tested cleaned the collars and cuifs of the soiled shirts,relative to the cleaning degree of a similar composition containing astandard detergent compound was considered a measure of the detergencyeffectiveness of the test compound.

The washing solution used in the test contained 0.03% organic surfaceactive agent and 0.06% sodium tripolyphosphate. (No fiuorescers orbleaches or antiredeposition agents were used.) The pH of the washingsolution was and water of 7 grains per gallon hardness was used. Aconventional, agitator-type washer was used. The detergent compound inthe standard detergent composition was sodium dodecylbenzenesulfonate,the most commonly used organic detergent compound in heavy duty laundrydetergent compositions. The test detergent composition contained thedetergent compound to be tested, i.e., compared with the standardcomposition.

Under these conditions, the detergency effectiveness ofbis(2-hydroxyethyl)dodecylamine oxide in wash water of 80 F. (l) wasquite superior to the detergency effectiveness of sodiumdodecylbenzenesulfonate at 140 F. and of dimethyldodecylamine oxide at80 F., and(2) was markedly superior to the detergency effectiveness ofsodium tallow alcohol sulfate and sodium dodecylbenzenesulfonate at 80F.

Thus, bis(2-hydroxyethyl)dodecylamine oxide showed surprising cool waterdetergency. Similar results are obtained with his (2 hydroxyethyl) 2hydroxytetradecylamine oxide, bis(2 hydroxyethyl) 2 hydroxydodecylamineoxide and N,N-bis(2-hydroxyethyl)-3-dodecoxy-2- hydroxypropylamineoxide.

Similar comparative results are obtained if, in the white shirtdetergency test, an organic alkaline sequestrant builder salt, sodiumethylenediaminetetraacetate or potassium nitriloacetate, is used insteadof the sodium tripolyphosphate.

Compounds wherein only one of the short chain N-substituents containhydroxy groups, e.g., (2-hydroxyethyl)- dodecylmethylamine oxide, alsoshow improved cool water detergency over the corresponding unsubstitutedcompounds and dodecylbenzenesulfonate but not to as great a degree asthe bis(2-hydroxyethyl) compounds.

The cool water detergency of those tertiary amine oxides of thisinvention wherein R and/or R (preferably both) contain a hydroxy groupis best seen in aqueous washing solutions where the temperature is inthe range of about 40 F. to about 95 F., the concentration of the activeamine oxide compound is in the range of about 0.005% to about 0.5% andthe washing solution also contains a water soluble alkaline inorganicbuilder salt or organic alkaline sequestrant builder salt (ashereinbefore described) in the range of about 0.01% to about 1.0%.Improved detergency is also seen using the amine oxide compositions ofthis invention in tepid (lukewarm) water (up to about 115 F.).

The tertiary amine oxides of this invention can be used in effectivesolid form detergent compositions having im proved hygroscopicity,thermal stability and cool water detergent characteristics. They havethe following formulas:

Spray-dried granular detergent Percent Bis(2-hydroxyethyl)dodecylarnineoxide 17.5 Sodium sulfate 23 Sodium tripolyphosphate 50 Sodium silicate6 Water 3.5

Granular detergent Percent (Z -hydroxyethyl)-2-hydroxydodecyl-ethylamineoxide 10 Sodium dodecylbenzenesulfonate (the dodecyl group being derivedfrom tetrapropylene) 10 Sodium nitrilo triacetate 50 Sodium sulfate 30Granular detergent Bis (2-hyrd oxypropyl tetradecylamine oxide 10Condensation product of one mole of n-onyl phenol and nine moles ofethylene oxide 10 Sodium pyrophosphate 50 Sodium carbonate 3 Trisodiumphosphate 3 Sodium sulfate 24 Milled toilet bar PercentBis(2-hydroxyethyl)alkylamine oxide, the alkyl group being derived fromcoconut fatty alcohol 10 Sodium coconut oil soap 15 Sodium tallow soap65 Moisture 10 Milled toilet bar N,N bis(2 hydroxyethyl) 3 dodecoxy 2hydroxypropylamine oxide 50 Tallow fatty acid 25 Moisture 15 Cornstarch5 Triethanolammonium ethylenediamine tetracetate 5 While the tertiaryamine oxides of this invention find particularly desirable utilizationin solid form detergent compositions because of their improvedhygroscopicity and thermal stability characteristics, the outstandingcool water detergency properties of the compounds provide basis fortheir advantageous use in liquid detergent compositions. Liquid formdetergent compositions provide convenience in use, particularly formeasurement and dis-. pensing operations. Liquid detergent compositionscan be in the form of solutions, dispersions or emulsions. Preferably,they can contain from about 2% to about 30% of the tertiary amine oxidesof this invention and from about 5% to about 40% of a water solubleinorganic alkaline builder salt or a water soluble organic alkalinesequestrant builder salt, the balance of the composition being asolvent, such as water, and/ or other liquid vehicles.

Examples of liquid detergent compositions having improved cool waterdetergency characteristics are as follows:

Liquid detergent What is claimed is:

1. Tertiary amine oxide compounds having the formula R R R N O, whereinR is selected from the group consisting of Z-hydroxyalkyl,3-hydroxyalkyl and 3-alkoxy-2- hydroxypropyl radicals in which the alkyland alkoxy, respectively, range in chain length from 10 to 18 carbonatoms, R and R are each selected from the group consisting of2-hydroxyethy1, 2-hydroxypropyl and 3-hydr-oxypropyl radicals.

2. Bis(2 hydroxyethyl) 2 hydroxytetradecylamine oxide.

3. N,N bis'(2 hydroxyethyl) 3 tetradecoxy 2- hydroxy propylamine oxide.

4. Bis(2 hydroxyethyl) 2 hydroxydodecylamine oxide.

5. Bis(2 hydroxyethyl) 3 hydroxydodecylamine oxide.

6. N,N bis(2 hydroxyethyl) 3 dodecoxy 2 hydroxypropylamine oxide.

References Cited by the Examiner UNITED STATES PATENTS 1,993,542 3/35Caspe 260-583 2,060,568 11/36 Graenacher et a1 260-583 References Citedby the Applicant UNITED STATES PATENTS 10 2,185,163 12/39 Ulrich.

Schoeller et a1.

FOREIGN PATENTS France.

15 CHARLES B. PARKER, Primary Examiner.

JULIUS GREENWALD, Examiner,

1. TERTIARY AMINE OXIDE COMPOUNDS HAVING THE FORMULA R1R2R3N-->O,WHEREIN R1 IS SELECTED FROM THE GROUP CONSISTING OF 2-HYDROXYALKYL,3-HYDROXYALKYL AND 3-ALKOXY-2HYDROXYPROPYL RADICALS IN WHICH THE ALKYLAND ALKOXY, RESPECTIVELY, RANGE IN CHAIN LENGTH FROM 10 TO 18 CARBONATOMS, R2 AND R3 ARE EACH SELECTED FROM THE GROUP CONSISTING OF2-HYDROXYETHYL, 2-HYDROXYPROPYL AND 3-HYDROXYPROPYL RADICALS.